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53185-12-9Relevant academic research and scientific papers
Concise and highly stereoselective syntheses of D-fagomine and 2-epi-fagomine
Kallam, Srinivasa Reddy,Datrika, Rajender,Khobare, Sandip R.,Gajare, Vikas S.,Rajana, Nagaraju,Mohan, H. Rama,Babu, J. Moses,Siddaiah,Pratap
, p. 1351 - 1353 (2018/03/23)
Highly stereoselective total syntheses of polyhydroxylated piperidines D-fagomine and 2-epi-fagomine have been developed starting from 3,4,6-tri-O-benzyl-D-glucal which is a derivative of D-Glucose. Key steps in the synthesis of these azasugars involved N-Boc-protected amine preparation from oxime followed by stereo specific iodination of alcohol and cascade cyclization triggered by N-Boc deprotection.
A PROCESS FOR SYNTHESIS OF PIPERIDINE ALKALOIDS
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, (2015/11/27)
The present invention discloses a process for synthesis of piperidine alkaloids selected from fagomine, 4-epi-fagomine and nojirimycin from tri-O-benzyl-D-glucal or tri-O-benzyl-D-galactal.
Transforming flask reaction into cell-based synthesis: Production of polyhydroxylated molecules via engineered Escherichia coli
Wei, Mohui,Li, Zijie,Li, Tiehai,Wu, Baolin,Liu, Yunpeng,Qu, Jingyao,Li, Xu,Li, Lei,Cai, Li,Wang, Peng George
, p. 4060 - 4065 (2015/11/11)
Dihydroxyacetone phosphate (DHAP)-dependent aldolases have been intensively studied and widely used in the synthesis of carbohydrates and complex polyhydroxylated molecules. However, strict specificity toward donor substrate DHAP greatly hampers their synthetic utility. Here, we transformed DHAP-dependent aldolases-mediated by in vitro reactions into bioengineered Escherichia coli (E. coli). Such flask-to-cell transformation addressed several key issues plaguing in vitro enzymatic synthesis: (1) it solves the problem of DHAP availability by in vivo-hijacking DHAP from the glycolysis pathway of the bacterial system, (2) it circumvents purification of recombinant aldolases and phosphatase, and (3) it dephosphorylates the resultant aldol adducts in vivo, thus eliminating the additional step for phosphate removal and achieving in vivo phosphate recycling. The engineered E. coli strains tolerate a wide variety of aldehydes as acceptor and provide a set of biologically relevant polyhydroxylated molecules in gram scale.
Applications and limitations of the I2-mediated carbamate annulation for the synthesis of piperidines: Five-versus six-membered ring formation
Corkran, Hilary M.,Munneke, Stefan,Dangerfield, Emma M.,Stocker, Bridget L.,Timmer, Mattie S. M.
, p. 9791 - 9802 (2013/10/22)
A protecting-group-free synthetic strategy for the synthesis of piperidines has been explored. Key in the synthesis is an I2-mediated carbamate annulation, which allows for the cyclization of hydroxy-substituted alkenylamines into piperidines, pyrrolidines, and furans. In this work, four chiral scaffolds were compared and contrasted, and it was observed that with both d-galactose and 2-deoxy-d-galactose as starting materials, the transformations into the piperidines 1-deoxygalactonorjirimycin (DGJ) and 4-epi-fagomine, respectively, could be achieved in few steps and good overall yields. When d-glucose was used as a starting material, only the furan product was formed, whereas the use of 2-deoxy-d-glucose resulted in reduced chemo- and stereoselectivity and the formation of four products. A mechanistic explanation for the formation of each annulation product could be provided, which has improved our understanding of the scope and limitations of the carbamate annulation for piperidine synthesis.
Total synthesis of d-fagomine and 6-deoxyfagomine
Min, Im Sook,Kim, Seung In,Hong, Seungmin,Kim, In Su,Jung, Young Hoon
, p. 3901 - 3906 (2013/06/27)
Total synthesis of d-fagomine and 6-deoxyfagomine from readily available d-lyxose is described. The key steps included regioselective and diastereoselective amination, hydroboration-oxidation, and Appel reaction. The reaction of 3,4-anti-tribenzyl ether with chlorosulfonyl isocyanate in toluene at 0 °C afforded 3,4-anti-amino alcohol, an essential compound for the preparation of d-fagomine and 6-deoxyfagomine, with a high diastereoselectivity (dr=26:1) in 74% yield. The origin of diastereoselectivity can be explained by the neighboring group effect, which leads to retention of the stereochemistry.
Assessment of partially deoxygenated deoxynojirimycin derivatives as glucosylceramide synthase inhibitors
Van Den Berg, Richard J. B. H. N.,Wennekes, Tom,Ghisaidoobe, Amar,Donker-Koopman, Wilma E.,Strijland, Anneke,Boot, Rolf G.,Van Der Marel, Gijsbert A.,Aerts, Johannes M. F. G.,Overkleeft, Herman S.
supporting information; experimental part, p. 519 - 522 (2011/09/15)
Glucosylceramide synthase (GCS) is an approved drug target for the treatment of Gaucher disease and is considered as a valid target for combating other human pathologies, including type 2 diabetes. The clinical drug N-butyldeoxynojirimycin (Zavesca) is thought to inhibit through mimicry of its substrate, ceramide. In this work we demonstrate that, in contrast to what is proposed in this model, the C2-hydroxyl of the deoxynojirimycin core is important for GCS inhibition. Here we show that C6-OH appears of less important, which may set guidelines for the development of GCS inhibitors that have less affinity (in comparison with Zavesca) for other glycoprocessing enzymes, in particular those hydrolases that act on glucosylceramide.
Efficient and stereoselective syntheses of DAB-1 and D-fagomine via chiral 1,3-oxazine
Kim, Ji-Yeon,Mu, Yu,Jin, Xiangdan,Park, Seok-Hwi,Pham, Van-Thoai,Song, Dong-Keun,Lee, Kee-Young,Ham, Won-Hun
, p. 9426 - 9432 (2011/12/14)
The concise, stereocontrolled syntheses of DAB-1 and d-fagomine were achieved utilizing chiral oxazine. The key features in these strategies are the stereoselective intramolecular oxazine formation catalyzed by palladium(0), and pyrrolidine and piperidine formation by catalytic hydrogenation of oxazine.
Synthesis of non-natural carbohydrates from glycerol and aldehydes in a one-pot four-enzyme cascade reaction
Babich, Lara,Van Hemert, Lieke J. C.,Bury, Aleksandra,Hartog, Aloysius F.,Falcicchio, Pierpaolo,Van Der Oost, John,Van Herk, Teunie,Wever, Ron,Rutjes, Floris P. J. T.
experimental part, p. 2895 - 2900 (2011/12/05)
A simple procedure has been developed for the synthesis of enantio- and diastereomerically pure carbohydrate analogues from glycerol and a variety of aldehydes in one pot using a four-enzyme cascade reaction. As a proof of concept of the usefulness of this enzymatic catalytic cascade the naturally occurring azasugar d-fagomine was synthesized. This work highlights the potential value of using enzymes in cascade reactions to selectively form complex products that by previous traditional organic chemistry could only be obtained via repeated isolation and purification of intermediates.
Silicon-mediated asymmetric synthesis of fagomine and 3,4-di-epi-fagomine
Kundu, Pintu K.,Ghosh, Sunil K.
, p. 1090 - 1096 (2011/10/04)
The synthesis of d-fagomine and its stereoisomer, d-3,4-di-epi-fagomine has been achieved from C2-symmetric 3,4-bis-silyl substituted adipic acid di-oxazolidin-2-one derivatives via stereocontrolled azidation and silicon to hydroxyl conversion as the key steps. The Evans oxazolidin-2-one controlled the stereochemical outcome of the azidation which supersedes the directing effects of the silyl substituent.
Efficient and stereodivergent syntheses of D- and L-fagomines and their analogues
Kumari, Nitee,Reddy, B. Gopal,Vankar, Yashwant D.
experimental part, p. 160 - 169 (2009/08/09)
The syntheses of D- and L-fagomines 1, 4, 5 and 6 and their isomers from starting D-glycals have been achieved. The syntheses involve elaboration of common amino alcohol precursors obtained from 2-deoxy-1-amino sugar derivatives. The key steps in the synt
